


Lady Luck & Her Birthday Blessings

by stunrunner



Category: Homestuck
Genre: Abusive Relationships, Crossdressing, Crossdressing Kink, Established Relationship, Lingerie, M/M, Mildly Dubious Consent, Oral Sex
Language: English
Status: Completed
Published: 2018-05-02
Updated: 2018-05-02
Packaged: 2019-05-01 01:20:20
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,459
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14509374
Author URL: https://archiveofourown.org/users/stunrunner/pseuds/stunrunner
Summary: Crowbar thinks he's on the way up, but really, he's just on the way back in.A prequel toHistory.





	Lady Luck & Her Birthday Blessings

**Author's Note:**

  * For [TwistaLolita](https://archiveofourown.org/users/TwistaLolita/gifts).



> Gonna be upfront, this fades to black before the sex gets good. I started writing this years ago when I knew a lot less about my own gender, and about gender in general, and I'm just not interested in continuing this anymore. Also, reader beware, Crowbar and Droog are not particularly progressive in their attitudes towards crossdressing, so if mention of that bothers you, probably skip this one. Thanks!

“Up here on the right, Itchy.” Crowbar had to brace a hand against the dash as the automobile jerked to a stop. He bit back a quip; no need to end a successful day on a sarcastic note. Plus, Itchy had done better than he'd expected in his first run as a getaway driver. Crowbar could give him a pass for tonight. “Thanks for the lift. Don't forget to swap the plates before you—”

Itchy waved a hand dismissively. “Yeah, yeah, I got it. See you tomorrow, boss.”

Crowbar watched him pull away from the curb. Boss. He savored the feel of the word, for once said without a mocking tone or a smirk. He supposed he really _was_ the boss, now. Well, he answered to Scratch of course, but Scratch wasn't around in the middle of a fire fight at Midnight National. He absently ran a finger over the thin red line on his neck. An inch to the left and the bullet would've gone straight through his carotid instead of grazing him, and he'd most likely have bled out on the floor of the bank before Stitch could fix it. _Happy birthday to me, from good ol' Lady Luck,_ he thought with a grin.

Crowbar whistled as he climbed to the seventh floor, the rickety wooden stairs creaking under his feet. He didn't mind this old place, but he sure would be glad when the mansion the Doc was building was done. Stairs aside, he was looking forward to living in the kind of place that _looked_ like a mob boss lived there.

He daydreamed about running this filthy city from a green throne as he let himself in, but froze three steps into the apartment, halfway through shrugging out of his coat.

A light was on around the corner, and there was a cooking smell he couldn't place in the air, as if his oven had recently been used for anything besides reheating old takeout. _Someone else is in here._

Slowly, he reached back and grabbed his crowbar, then crept towards the rectangle of bright light in the otherwise dark room. Shit, could whoever it was hear his heart knocking hard against his ribcage with every beat? Crowbar paused against the wall next to the door frame for just a moment. _You wanted to be the boss,_ he reminded himself ruefully. _Head honchos get power, money, lackeys... And enemies._

Before he could lose his nerve, he whipped across the threshold into the kitchen, clutching the red bar tightly. He barely processed the dark person-shape standing at the counter before he vaulted over a chair, swung the crowbar in a narrow arc, and pulled it in against the intruder's throat. The momentum from his dash pushed his would-be assailant's face against the cabinets as Crowbar held the hard crimson steel tightly against his windpipe.

“Who the fuck are you?” he demanded in a higher pitch than he would've liked. “How did you get in?”

Before he even considered that he would have to relax his choke-hold to get any answers, Crowbar realized several things simultaneously. First, the intruder was several inches taller than he was. The slender frame Crowbar was pressed to, chest-to-back, was not tight with the tension of an unexpected assault, but rather loose, relaxed. At ease. The jacket covering that back was elegantly tailored, even to Crowbar's inexpert eye, skimming just so over the man's flanks. And lastly, he smelled strongly of cigarette smoke. Not just any cigarette, either—Derse Blacks. An expensive brand that Crowbar had smelled just one place before, one place that made the scent hone in on a primal memory, one that make him release the “intruder” and spring back, bumping the back of his thighs against the table.

“Diamonds?!” he said, unable to stop his jaw from dropping just a little as he caught his balance. “What the blue blazes are you doing here?”

Droog lightly probed with long, elegant fingers at the cheekbone that had been so rudely slammed into the cabinet. “Your locks are better than you'd expect in... a place like this,” he said, the pause speaking volumes about his disdain for the apartment, “but hardly good enough to warrant such surprise.” Finding minimal damage, he gestured to the table expectantly.

Crowbar couldn't help it; with the adrenaline still pounding through his veins, he whirled around expecting... Well, he didn't know quite what. But certainly not a classy table setting—where had those dishes even come from? Crowbar didn't think he owned any two matching pieces of flatware, let alone a full complement of silverware—a bottle of expensive red wine breathing in a crystal decanter, and several platters of expertly plated food he couldn't identify but would bet his life was famed for being both exceptionally delicious and exceptionally expensive.

A pair of thin lips just barely brushed the back of Crowbar's neck as he took in the spread. “Shall we?” Droog murmured as he crossed to pull out a chair.

Crowbar was tempted to roll his eyes, but the food _did_ look good, so he stifled his natural smart-ass impulses and sat. “Thanks. It's one heck of a birthday present for a guy you haven't seen in... What's it been, seven weeks now? Eight?” Well, _most_ of his smart-ass impulses, anyway.

Droog took his own seat, pulling the cloth napkin at his setting into his lap. “Oh, your present comes after dinner,” he said as he began to transfer some of the dainty morsels to his plate.

Crowbar's eyebrows rose. “If this is just the appetizer, that's gotta be one hell of a dessert.”

His heartbeat accelerated again when the corners of Droog's mouth twitched upward, the equal of a wicked grin in a less-composed man. “You could say that.” Crowbar couldn't decide if the flutter in his stomach was nervousness or excitement. Probably both.

Either way, he wasn't going to let Droog dodge the real question. He didn't touch the food. “Two months, Droog,” he said bluntly. “You disappeared. Where the hell were you?”

“Let's not talk about work over dinner, shall we?”

Crowbar blinked. “You were on a job?” he asked. “Why didn't you tell me?” he added before he could stop himself, wincing almost as the words came out of his mouth. He sighed. “Never mind. Stupid question, I guess.”

Droog said nothing; he didn't have to.

“Still,” Crowbar tried, “you could at least—”

“Crowbar. Eat.” Droog's command was congenial, delivered in a tone no harsher than his normal conversational voice, but with such a clear expectation of obedience that Crowbar found himself reaching for a serving spoon without thinking. He almost pulled back, but with Droog's eyes on him, the gesture would have seemed petulant or ungrateful, and he _was_ hungry. He helped himself to a little bit of everything, and started to tell Diamonds what he'd missed over the last two months. _The important thing is that he's back now,_ he reminded himself. _He even remembered my birthday._

Crowbar's intuition about the food had been correct—it was all exquisite. He knew his palate was far from Droog's level of refinement, but even he could appreciate the complexity of the flavors, the delicate textures, and the way every element of each dish complemented every other element perfectly.

His appreciation of the meal was itself complemented by his appreciation of Diamonds as they ate. Crowbar was careful not to stare or let the conversation lag, but he felt a different kind of hunger at the graceful twist of Droog's wrist to finish pouring the wine without it dripping down the side of the decanter, the precise efficiency with which he stripped meat off of the bones, the way his dark eyes skewered Crowbar to the chair like a pinned butterfly with their intensity. He felt Droog's gaze crawling over every inch of him, noticing and cataloging every movement. After being alone at home for so long, the quiet scrutiny felt ten times as intense as before. He felt a prickling, hot flush slowly spreading from his face down the rest of his body, one that had nothing to do with the wine. He shifted his legs slightly in an attempt to conceal the slight tenting of his green slacks; Droog didn't react, but Crowbar was impossibly sure he'd noticed and known why he'd moved, which didn't help the trouser situation one bit. Worse, he couldn't stop wondering what his “present” was, or why Droog had allowed himself such a naked look of anticipation earlier.

By the time they put their forks and knives down on empty plates and poured the last of the wine, Crowbar's pulse was throbbing hard in his ears once again. One hand fidgeted with the corner of his napkin, while the other idly swirled the liquid in his glass. 

To a casual observer, Droog would seem completely oblivious to his companion's nervousness. He was certainly in no hurry, taking his time with languorous sips of the merlot. But even if Crowbar didn't know him well enough to watch his eyes linger at Crowbar's neck or the red spots still blooming on his cheeks, he could feel the smugness radiating off Droog as he noted all the little tells of anxiety. _You don't have any secrets from him,_ Crowbar thought, and despite—because of?—the frustration of that helplessness, his cock twitched.

Droog drained the last of his wine, and the instant the bottom of the glass touched the table, Crowbar's resolve snapped. “So, I think I recall there being a present of some kind mentioned earlier?” he asked, trying for nonchalance. Trying, and failing miserably. Even he could hear the husky, desperate edge in his voice.

Droog chuckled. “A valuable lesson for a newly risen leader,” he said as he rose from his seat. “The man who speaks first, loses.”

“Horse-hockey, you're fetching the present, aren't you?” Crowbar asked with a raised eyebrow.

Droog took his hand, his touch sending tingling electric sparks down the hypersensitive skin of Crowbar's arm, and pulled him out of his chair. “I'm bringing you to it, actually,” he said as he led them through the apartment, “but we'll both remember that you had to ask.”

Crowbar was half-debating to himself whether or not it counted as “asking” to pose the question of why that mattered before the realization that they were heading towards the bedroom hit him and drove less-important thoughts out of his mind. Some tiny, lucid corner of him insisted that he shouldn't forgive Droog so easily, that he shouldn't get to just breeze in and out of his life whenever it was convenient for him. Its protests were too quiet and timid to overrule the needy heat building in his groin.

He let Droog usher him into the bedroom, and heard the faint click of the door locking behind them as his eyes fell on a single neatly-wrapped rectangular box on the bed. Red wrapping paper, of course, with a thick black ribbon tied in an elegant bow. Crowbar absently wondered if Droog had tied it himself.

He looked back, but Droog was just leaning back against the closed door with his arms folded. His long limbs were seemingly relaxed, but his eyes had that sharp, hungry glint—it reminded him of a shark's eyes as it circled its prey, the anticipation building at the scent of blood in the water. At the scent of fear. Crowbar had opened his mouth to make some wisecrack about the wrapping, but that look dried his throat in more ways than one. He turned back to the present without a word.

The black bow came undone with one tug of the ribbon's end, of course. He hesitated before lifting the lid— _what the Sam Hill could possibly be worth all this build-up?_ —but his curiosity swiftly overcame his nervousness, and he pulled it off to reveal...

...A complete mix-up, apparently.

He raised his eyebrows looking at Droog. “Gosh, it's lovely, but I don't think it's my size,” he deadpanned, picking up the lacy maroon bra by the straps on his outstretched index fingers. “But really, Droog, much as I want to know what my present is, who the hell did you even get this for? I didn't think you—”

“Check again,” Droog interrupted, pushing off of the door to stand behind where Crowbar sat on the edge of the bed.

“Check what? I mean, this is obviously the wrong—”

“The size.”

He blinked. “40A? What does that have to do with... aaahhhh,” he trailed off as a row of razor-sharp teeth skimmed lightly over the skin of his neck, just under his jawline. He'd already been half-hard, but his cock practically leapt to attention as Droog left a new set of faint red lines of just-barely-unbroken skin almost parallel to the deeper track left by the bullet earlier that evening.

Droog paused to stroke his thumb down that track, pressing just hard enough that Crowbar held in a hiss of discomfort. “Getting sloppy in your old age?” he teased, his hot breath tickling against the back of Crowbar's neck.

“Let's not talk about work, shall we?” Crowbar parroted.

Droog's hands trailed over the green fabric covering his shoulders, then back up to the front of his neck. _He's going to choke me,_ Crowbar thought with a spike of adrenaline that sent his pulse racing even faster even as he sat there, paralyzed. How many other lives had those hands taken? _Oh Jesus, I always have to run my goddamn mouth and now they're going to find my dead body next to a box of ladies' underwear—_

But rather than darting to squeeze his carotid arteries shut, Droog merely tugged at his bowtie. There was a small vexed noise in his ear when it didn't fall apart as easily as the present's bow had, and then both hands were working to untie it and to begin to undo his buttons. Crowbar sagged slightly in relief and perhaps a little disappointment. _Wait, disappointment? That he didn't, what, kill me? What the fuck?_

Droog's warm mouth on the back of his neck thankfully derailed that train of thought immediately, and Crowbar bit his lip to stop from moaning. How could the bastard still push all his buttons perfectly after disappearing for two months to god knows where? Speaking of which...

“You still haven't told me, mm, what my real present is,” he reminded Droog, though he didn't stop him from pulling his shirt off and folding it neatly beside them on the bed.

“'Real'?” In his mind's eye, Crowbar could see Droog behind him raising his eyebrows just a fraction in feigned innocence. His hands traced over Crowbar's sides; the muscles there were tensed piano-wire taut just from a tweak of his nipple here, a kiss to the shoulder blade at just the right moment. He sucked in a sharp breath when the side of Droog's hand “accidentally” brushed against the uncomfortably confined bulge of his slacks as he started to unbutton them.

“Yes, real.” It was so hard to focus with Droog's fingers working just inches away from his cock, but unaccounted-for lingerie was just barely enough to take off the edge. “It's not like you want ME to wear the—

“Oh goddammit,” he said as suddenly everything clicked into place, and he _really_ hoped it was Droog's teeth on his collarbone that was making his dick throb, because otherwise he was going to need a _lot_ more wine. “You can't expect—”

Droog cut off his protest by turning Crowbar to face him and pushing against him with a vicious, biting kiss. Crowbar hated how he gasped for breath when Droog pulled away. “I can,” he said, “and I will.” He leaned in against Crowbar, the silky fabric of his expensive trousers rubbing deliberately against the bare expanse of Crowbar's thigh. Wait, when did his pants get pushed down to his knees?

“Darling,” Droog whispered in his ear, his voice like a knife sliding down silk. “Don't you trust me?” A mocking tongue traced its way from his mouth, down his chest, to the top of his thigh, and Crowbar shivered.

_No,_ he wanted to scream, _of course I don't trust you, or at least I shouldn't, and you_ know _that, but—_

“Well?” Droog interrupted his inner monologue of paralysis, teasingly tugging at the waistband of his boxers. He looked up, and Crowbar saw his own desire mirrored in those flat, nearly-black eyes. He could almost see the whirring gears behind that stare, the eerily accurate balances that weighed his own motivations, wants, and worth, which just made the predatory animality of his gaze even more unsettling.

And, unfortunately for Crowbar, even more attractive.

He inclined his head the barest fraction that could still be called a nod, and the moment he moved, Droog pulled his boxers down to his ankles in one fluid motion. Crowbar had half a second to fume ( _Of course HIS clothes get the royal treatment but he doesn't give a rat's ass if he tears MINE to shreds_ ) before Droog's tongue stilled all thought, licking a stripe up the bottom of his shaft from base to head. He closed his eyes and leaned back a little on the edge of the bed, parting his thighs wider to give easier access, but Droog continued to tease him with long, slow swipes that ended in shuddering swirls around his tip.

Crowbar opened his eyes when he heard the tissue paper rustling to his right. Without slowing his ministrations, Droog had pulled over the gift box and taken out the flimsy patch of fabric on strings that he guessed qualified as underwear.

“Do we really have to—” Crowbar started, but his objection choked into nothingness as Droog abruptly took his entire cock into his mouth, all the way to the base. “Fuck,” he gasped, only half aware of Droog moving his legs around as he slowly, so tantalizingly slowly, slid his mouth back.

The little pop of suction as Droog pulled away from the head of his dick was echoed by the snap of a thin band of elastic and lace on his hipbone, making Crowbar flinch. “There,” Droog practically purred as he deftly tucked Crowbar's cock into the panties and caressed his thighs. 

“Seems more like a present for you, so far,” Crowbar said as Droog picked up the bra from the box. “You're really into this?”

Droog shifted behind him again, cupping between Crowbar's legs with one hand while the other started to work his arms into the loops of the bra straps. “Am I the only one?”

“Hey, I'm into you touching me, not—” He cut off with a groan as Droog pulled and rubbed the silk over his head with a thumb. 

After luxuriating in Droog's expert touch for a few moments, Crowbar raised his head from where it was lolling on Droog's shoulder to look down while he worked. He had to admit, he could see what the other man was enjoying. There was something pleasantly... exotic about the sight: the maroon fabric straining around the bulge of his stiff shaft, lifting the strings off the thong off of his hipbones, the blood-red color a flattering contrast with the dark skin of Droog's hand. The odd slippery friction of the panties bunching and sliding around his cock as Droog pumped it didn't hurt either. 

Crowbar stifled a whimper as Droog withdrew his hand to fasten and adjust the bra. He squirmed a little at the tightness of the band around his ribcage, not constricting enough to interfere with his breathing, but enough to feel foreign and uncomfortable. Rather than molded form cups jutting into empty air, little triangular slips of sheer nylon covered his nipples. The straps slipped down his shoulders before he felt Droog slide something on the strap, pulling it properly flush against his skin. 

Crowbar rolled his shoulders a few times, trying to adjust to the feel of the undergarment. He focused on the oddity of the physical sensations, trying to push the more metaphysical connotations of his ensemble out of his mind. _It's not “ladies” underwear if a man is wearing it, right?_ he rationalized to himself. “It feels like I'm wearing a damn plow harness or something,” he said aloud as he tugged at the band in a futile attempt to make it feel less like... well, like a bra.

Suddenly, the bra _pulled_ and he was yanked backwards onto the bed. Before he could process what had happened, Droog was straddling him and leaning down, his forearms pinning Crowbar to the bed by the shoulders. “Well, aren't you?” he said smugly as he rolled his hips slowly against Crowbar.


End file.
